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Review

Non-peptide δ opioid agonists and antagonists (Part II)

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Pages 353-374 | Published online: 25 Feb 2005

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Hideaki Fujii, Toshihiro Takahashi & Hiroshi Nagase. (2013) Non-peptidic δ opioid receptor agonists and antagonists (2000 – 2012). Expert Opinion on Therapeutic Patents 23:9, pages 1181-1208.
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RW Clarke. (2000) Synaptic mechanisms in nociception: emerging targets for centrally-acting analgesics. Emerging Therapeutic Targets 4:2, pages 173-189.
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Articles from other publishers (37)

Donald J. AbrahamChristopher R. McCurdy & Thomas E. Prisinzano. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 1 171 .
Kohei Hayashida, Shigeto Hirayama, Takashi Iwai, Yoshikazu Watanabe, Toshihiro Takahashi, Junichi Sakai, Eriko Nakata, Tomio Yamakawa, Hideaki Fujii & Hiroshi Nagase. (2017) Novel delta opioid receptor agonists with oxazatricyclodecane structure showing potent agonistic activities. Bioorganic & Medicinal Chemistry Letters 27:12, pages 2742-2745.
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Giovanni Loriga, Paolo Lazzari, Ilaria Manca, Stefania Ruiu, Matteo Falzoi, Gabriele Murineddu, Mirko Emilio Heiner Bottazzi, Giovanni Pinna & Gérard Aimè Pinna. (2015) Novel diazabicycloalkane delta opioid agonists. Bioorganic & Medicinal Chemistry 23:17, pages 5527-5538.
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Toru Nemoto, Yusuke Iihara, Shigeto Hirayama, Takashi Iwai, Eika Higashi, Hideaki Fujii & Hiroshi Nagase. (2015) Naltrindole derivatives with fluorinated ethyl substituents on the 17-nitrogen as δ opioid receptor inverse agonists. Bioorganic & Medicinal Chemistry Letters 25:15, pages 2927-2930.
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Hideaki Fujii, Kohei Hayashida, Akiyoshi Saitoh, Akinobu Yokoyama, Shigeto Hirayama, Takashi Iwai, Eriko Nakata, Toru Nemoto, Yuka Sudo, Yasuhito Uezono, Mitsuhiko Yamada & Hiroshi Nagase. (2014) Novel Delta Opioid Receptor Agonists with Oxazatricyclodecane Structure. ACS Medicinal Chemistry Letters 5:4, pages 368-372.
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Giovanni Loriga, Paolo Lazzari, Stefania Ruiu, Giorgio Marchese, Ilaria Manca, Gian Luca Casu, Christian Dessì, Gérard Aimè Pinna, Battistina Asproni & Gabriele Murineddu. (2013) Synthesis and biological evaluation of novel delta (δ) opioid receptor ligands with diazatricyclodecane skeletons. European Journal of Medicinal Chemistry 69, pages 413-426.
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Donald J. AbrahamChristopher R. McCurdy & Thomas E. Prisinzano. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 569 736 .
Silvia N. Calderon. 2011. Chemistry of Opioids. Chemistry of Opioids 121 140 .
Ralph Holl, Bettina Jung, Dirk Schepmann, Hans-Ulrich Humpf, Renate Grünert, Patrick J. Bednarski, Werner Englberger & Bernhard Wünsch. (2009) Synthesis and Pharmacological Evaluation of SNC80 Analogues with a Bridged Piperazine Ring. ChemMedChem 4:12, pages 2111-2122.
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. (2008) 3D Quantitative and Qualitative Structure-Activity Relationships of the δ -Opioid Receptor Antagonists. Bulletin of the Korean Chemical Society 29:3, pages 656-662.
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Matthew D. Metcalf & Andrew Coop. (2007) 5′-Halogenated analogs of oxymorphindole. Bioorganic & Medicinal Chemistry Letters 17:21, pages 5916-5917.
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Kejun Cheng, In Jong Kim, Mei-Jing Lee, Steven A. Adah, Tyler J. Raymond, Edward J. Bilsky, Mario D. Aceto, Everette L. May, Louis S. Harris, Andrew Coop, Christina M. Dersch, Richard B. Rothman, Arthur E. Jacobson & Kenner C. Rice. (2007) Opioid ligands with mixed properties from substituted enantiomeric N -phenethyl-5-phenylmorphans. Synthesis of a µ-agonist δ-antagonist and δ-inverse agonists . Organic & Biomolecular Chemistry 5:8, pages 1177-1190.
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Denzil Bernard, Andrew Coop & Alexander D. MacKerell. (2007) Quantitative Conformationally Sampled Pharmacophore for δ Opioid Ligands:  Reevaluation of Hydrophobic Moieties Essential for Biological Activity. Journal of Medicinal Chemistry 50:8, pages 1799-1809.
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Eyup Akgün, Philip S. Portoghese, Munawwar Sajjad & Hani A. Nabi. (2007) Synthesis and 124 I‐labeling of m ‐iodophenylpyrrolomorphinan as a potential PET imaging agent for delta opioid (DOP) receptors . Journal of Labelled Compounds and Radiopharmaceuticals 50:3, pages 165-170.
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Bertrand Le Bourdonnec, Allan J. Goodman, Mathieu Michaut, Hai-Fen Ye, Thomas M. Graczyk, Serge Belanger, Torsten Herbertz, Glenn P. A. Yap, Robert N. DeHaven & Roland E. Dolle. (2006) Elucidation of the Bioactive Conformation of the N -Substituted trans -3,4-Dimethyl-4-(3-hydroxyphenyl)piperidine Class of μ-Opioid Receptor Antagonists . Journal of Medicinal Chemistry 49:25, pages 7278-7289.
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James B. Thomas, Li Zhang, Hernán A. Navarro & F. Ivy Carroll. (2006) Highly Potent and Selective Phenylmorphan-Based Inverse Agonists of the Opioid δ Receptor. Journal of Medicinal Chemistry 49:18, pages 5597-5609.
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Andrés A. Trabanco, Shirley Pullan, José M. Alonso, Rosa M. Alvarez, José I. Andrés, Inge Boeckx, Javier Fernández, Antonio Gómez, Laura Iturrino, Frans E. Janssens, Joseph E. Leenaerts, Ana I. De Lucas, Encarna Matesanz, Theo Meert & Thomas Steckler. (2006) 4-Phenyl-4-[1H-imidazol-2-yl]-piperidine derivatives, a novel class of selective δ-opioid agonists. Bioorganic & Medicinal Chemistry Letters 16:1, pages 146-149.
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Bettina Jung, Werner Englberger & Bernhard Wünsch. (2005) Molecular modeling directed synthesis of a bicyclic analogue of the δ opioid receptor agonist SNC 80. Archiv der Pharmazie 338:5-6, pages 281-290.
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Sanjay K. Srivastava, Shefali, Carl N. Miller, Mario D. Aceto, John R. Traynor, John W. Lewis & Stephen M. Husbands. (2004) Effects of Substitution on the Pyrrole N Atom in Derivatives of Tetrahydronaltrindole, Tetrahydrooxymorphindole, and a Related 4,5-Epoxyphenylpyrrolomorphinan. Journal of Medicinal Chemistry 47:26, pages 6645-6648.
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Steven J. Coats, Mark J. Schulz, John R. Carson, Ellen E. Codd, Dennis J. Hlasta, Philip M. Pitis, Dennis J. StoneJr.Jr., Sui-Po Zhang, Ray W. Colburn & Scott L. Dax. (2004) Parallel methods for the preparation and SAR exploration of N-ethyl-4-[(8-alkyl-8-aza-bicyclo[3.2.1]oct-3-ylidene)-aryl-methyl]-benzamides, powerful mu and delta opioid agonists. Bioorganic & Medicinal Chemistry Letters 14:22, pages 5493-5498.
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John R Carson, Steven J Coats, Ellen E Codd, Scott L Dax, Jung Lee, Rebecca P Martinez, Lou Anne Neilson, Philip M Pitis & Sui-Po Zhang. (2004) N , N -Dialkyl-4-[(8-azabicyclo[3.2.1]-oct-3-ylidene)phenylmethyl]benzamides, potent, selective δ opioid agonists. Bioorganic & Medicinal Chemistry Letters 14:9, pages 2109-2112.
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F. Ivy Carroll, Li Zhang, S. Wayne Mascarella, Hernán A. Navarro, Richard B. Rothman, Buddy E. Cantrell, Dennis M. Zimmerman & James B. Thomas. (2003) Discovery of the First N-Substituted 4β-Methyl-5-(3-hydroxyphenyl)morphan To Possess Highly Potent and Selective Opioid δ Receptor Antagonist Activity. Journal of Medicinal Chemistry 47:2, pages 281-284.
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In Jong Kim, Thomas Ullrich, James W. Janetka, M.Scott Furness, Arthur E. Jacobson, Richard B. Rothman, Christina M. Dersch, Judith L. Flippen-Anderson, Clifford George & Kenner C. Rice. (2003) Diaryldimethylpiperazine ligands with μ- and δ-opioid receptor affinity: Synthesis of (+)-4-[(αR)-α-(4-allyl-(2S,5S)-dimethylpiperazin-1-yl)-(3-hydroxyphenyl)methyl]-N-ethyl-N-phenylbenzamide and (−)-4-[(αR)-α-(2S,5S)-dimethylpiperazin-1-yl)-(3-hydroxyphenyl)methyl]-N-ethyl-N-phenylbenzamide. Bioorganic & Medicinal Chemistry 11:22, pages 4761-4768.
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Nicolas Marie, Gérard Landemore, Claire Debout, Philippe Jauzac & Stéphane Allouche. (2003) Pharmacological characterization of AR-M1000390 at human delta opioid receptors. Life Sciences 73:13, pages 1691-1704.
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F. Ivy Carroll. (2003) 2002 Medicinal Chemistry Division Award Address:  Monoamine Transporters and Opioid Receptors. Targets for Addiction Therapy. Journal of Medicinal Chemistry 46:10, pages 1775-1794.
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Denzil Bernard, Andrew Coop & Alexander D. MacKerell. (2003) 2D Conformationally Sampled Pharmacophore:  A Ligand-Based Pharmacophore To Differentiate δ Opioid Agonists from Antagonists. Journal of the American Chemical Society 125:10, pages 3101-3107.
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Donald J. AbrahamJane V. Aldrich & Sandra C. Vigil‐Cruz. 2003. Burger's Medicinal Chemistry and Drug Discovery. Burger's Medicinal Chemistry and Drug Discovery 331 482 .
L Verotta, F Orsini, M Sbacchi, M.A Scheildler, T.A Amador & E Elisabetsky. (2002) Synthesis and antinociceptive activity of chimonanthines and pyrrolidinoindoline-Type alkaloids. Bioorganic & Medicinal Chemistry 10:7, pages 2133-2142.
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Thomas Ullrich, Christina M Dersch, Richard B Rothman, Arthur E Jacobson & Kenner C Rice. (2001) Derivatives of 17-(2-methylallyl)-substituted noroxymorphone: variation of the delta address and its effects on affinity and selectivity for the delta opioid receptor. Bioorganic & Medicinal Chemistry Letters 11:21, pages 2883-2885.
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James B. Thomas, Xavier M. Herault, Richard B. Rothman, Robert N. Atkinson, Jason P. Burgess, S. Wayne Mascarella, Christina M. Dersch, Heng Xu, Judith L. Flippen-Anderson, Clifford F. George & F. Ivy Carroll. (2001) Factors Influencing Agonist Potency and Selectivity for the Opioid δ Receptor Are Revealed in Structure−Activity Relationship Studies of the 4-[( N- Substituted-4-piperidinyl)arylamino]- N,N- diethylbenzamides . Journal of Medicinal Chemistry 44:6, pages 972-987.
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Anthony L Vaccarino & Abba J Kastin. (2000) Endogenous opiates: 1999. Peptides 21:12, pages 1975-2034.
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Andrew Coop, Arthur E Jacobson, Mario D Aceto, Louis S Harris, John R Traynor, James H Woods & Kenner C Rice. (2000) N-cyclohexylethyl-N-noroxymorphindole: a μ-Opioid preferring analogue of naltrindole. Bioorganic & Medicinal Chemistry Letters 10:21, pages 2449-2451.
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Niklas Plobeck, Daniel Delorme, Zhong-Yong Wei, Hua Yang, Fei Zhou, Peter Schwarz, Lars Gawell, Hélène Gagnon, Benjamin Pelcman, Ralf Schmidt, Shi Yi Yue, Christopher Walpole, William Brown, Edward Zhou, Maryse Labarre, Kemal Payza, Stephane St-Onge, Augustus Kamassah, Pierre-Emmanuel Morin, Denis Projean, Julie Ducharme & Edward Roberts. (2000) New Diarylmethylpiperazines as Potent and Selective Nonpeptidic δ Opioid Receptor Agonists with Increased In Vitro Metabolic Stability. Journal of Medicinal Chemistry 43:21, pages 3878-3894.
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Dean Y Maeda & Andrew Coop. (2000) Studies into the Direct Conversion of Indolomorphinans to their 4-Phenolic Derivatives. Tetrahedron 56:38, pages 7399-7402.
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James B Thomas, Robert N Atkinson, Richard B Rothman, Jason P Burgess, S.Wayne Mascarella, Christina M Dersch, Heng Xu & F.Ivy Carroll. (2000) 4-[(8-Alkyl-8-azabicyclo[3.2.1]octyl-3-yl)-3-arylanilino]- N , N -diethylbenzamides: high affinity, selective ligands for the delta opioid receptor illustrate factors important to antagonist activity. Bioorganic & Medicinal Chemistry Letters 10:11, pages 1281-1284.
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Robert E. Boyd, John R. Carson, Ellen E. Codd, A.Diane Gauthier, Lou Anne Neilson & Sui-Po Zhang. (2000) Synthesis and binding affinities of 4-diarylaminotropanes, a new class of delta opioid agonists. Bioorganic & Medicinal Chemistry Letters 10:10, pages 1109-1111.
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Josue Alfaro-Lopez, Toru Okayama, Keiko Hosohata, Peg Davis, Frank Porreca, Henry I. Yamamura & Victor J. Hruby. (1999) Exploring the Structure−Activity Relationships of [1-(4- tert -Butyl-3‘-hydroxy)benzhydryl-4-benzylpiperazine] (SL-3111), A High-Affinity and Selective δ-Opioid Receptor Nonpeptide Agonist Ligand . Journal of Medicinal Chemistry 42:26, pages 5359-5368.
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